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3-hydroxypyridine compound and its preparation method and pharmaceutical use

一种化合物、药学的技术，应用在医药领域，能够解决半衰期短、病患大负担、EPO使用费用高等问题

Active Publication Date: 2016-11-23
SHENYANG SUNSHINE PHARMA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, as the production and application of EPO have been greatly developed, exogenous EPO still faces several problems: 1. The cost of using EPO is relatively high, especially for patients who need long-term use.
2. As a macromolecular glycoprotein, EPO also has the characteristics of low bioavailability, short half-life in vivo, and easy hydrolysis by enzymes in the gastrointestinal tract. Therefore, EPO must be injected frequently, which limits the patient's self-medication The possibility of this has brought great inconvenience to the patient
3. The industrially synthesized EPO still cannot avoid the problem of immunogenicity, and the product has a certain risk of drug use

Method used

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  • 3-hydroxypyridine compound and its preparation method and pharmaceutical use
  • 3-hydroxypyridine compound and its preparation method and pharmaceutical use
  • 3-hydroxypyridine compound and its preparation method and pharmaceutical use

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0053]

[0054] 2-(3-Hydroxy-5-phenoxy-2-pyridinecarboxamido)acetic acid (Compound No. 1)

[0055] Step 1: Preparation of 5-bromo-3-methoxypyridine-2-carbonitrile

[0056] A solution of sodium methoxide (9.7 g, 0.18 mol) in methanol (50 ml) was added dropwise to a suspension of 5-bromo-3-fluoropyridine-2-carbonitrile (30 g, 0.15 mol) in methanol (150 ml) at room temperature. After the dropwise addition was completed, the reaction solution became clear after reacting at room temperature for 2 hours. Add a small amount of glacial acetic acid to the reaction solution to adjust the pH to 7-8, add ice water (300ml), concentrate the reaction solution until solids precipitate, then cool and stand for 2 hours to make the solids precipitate more thoroughly. The precipitated solid was suction-filtered, the filter cake was washed with water, and the filter cake was collected and air-dried at room temperature to obtain a white solid 5-bromo-3-methoxypyridine-2-carbonitrile (24 g, yiel...

Embodiment 2

[0066]

[0067] 2-(5-(2,3-Dimethylphenoxy)-3-hydroxypyridine-2-carboxamido)acetic acid (Compound No. 5)

[0068] Step 1: Preparation of 5-bromo-3-methoxypyridine-2-carbonitrile

[0069] A solution of sodium methoxide (9.7 g, 0.18 mol) in methanol (50 ml) was added dropwise to a suspension of 5-bromo-3-fluoropyridine-2-carbonitrile (30 g, 0.15 mol) in methanol (150 ml) at room temperature. After the dropwise addition was completed, the reaction solution became clear after reacting at room temperature for 2 hours. Add a small amount of glacial acetic acid to the reaction solution to adjust the pH to 7-8, add ice water (300ml), concentrate the reaction solution until solids precipitate, then cool and stand for 2 hours to make the solids precipitate more thoroughly. The precipitated solid was suction-filtered, the filter cake was washed with water, and the filter cake was collected and air-dried at room temperature to obtain a white solid 5-bromo-3-methoxypyridine-2-carbonitri...

Embodiment 3

[0079]

[0080] 2-(5-(3-Chlorophenoxy)-3-hydroxypyridine-2-carboxamido)acetic acid (Compound No. 22)

[0081] Step 1: Preparation of 5-bromo-3-methoxypyridine-2-carbonitrile

[0082] A solution of sodium methoxide (9.7 g, 0.18 mol) in methanol (50 ml) was added dropwise to a suspension of 5-bromo-3-fluoropyridine-2-carbonitrile (30 g, 0.15 mol) in methanol (150 ml) at room temperature. After the dropwise addition was completed, the reaction solution became clear after reacting at room temperature for 2 hours. Add a small amount of glacial acetic acid to the reaction solution to adjust the pH to 7-8, add ice water (300ml), concentrate the reaction solution until solids are precipitated, then cool and stand for 2 hours to make the solids precipitate more thoroughly. The precipitated solid was suction-filtered, the filter cake was washed with water, and the filter cake was collected and air-dried at room temperature to obtain a white solid 5-bromo-3-methoxypyridine-2-carbonit...

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PUM

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Abstract

The invention relates to a compound shown in the formula (I) or its pharmaceutically acceptable salt, wherein R1 and R2 respectively represent hydrogen, R3 represents hydrogen or C1-C7 straight chain, branched chain or annular alkyl, and R4, R5, R6, R7 and R8 respectively represent C1-C7 alkyl or halogenated C1-C7 alkyl. The invention also relates to a preparation method of the compound, a pharmaceutical composition containing the compound or its pharmaceutically acceptable salt, and a use of the compound or its pharmaceutically acceptable salt in preparation of a drug for inhibiting HIF prolyl hydroxylase or a drug for promoting endogenous EPO generation.

Description

technical field [0001] The present invention relates to the field of medicine, specifically, the present invention relates to 3-hydroxyl compounds, the preparation method of said compound, and its use in the preparation of drugs for inhibiting the activity of ischemia-inducible factor (HIF) proline hydroxylase application. Background technique [0002] Hypoxia inducible factor (HIF) is a transcriptional activator containing basic helix-loop-helix (bHLH) and PAS (Per / Arnt / Sim), which mediates a series of genes in biological cells Regulation in response to cellular hypoxia. (Chowdhury, R., Hardy, A and Schofield, C.J., The human oxygen sensing machinery and its manipulation, Chem.Soc.Rev., 2008, 37, pp. 1308-1319; Kaelin , W.G., Jr., and Ratcliffe, P.J., Oxygen sensing by metazoans: the central role of the HIF hydroxylase pathway (Oxygen sensing by metazoans: the central role of the HIF hydroxylase pathway) Moore. Cell, 2008, 30, 393 - 402 pages; Schofield, C.J., and Ratcli...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/81A61K31/44A61P43/00A61P7/00A61P19/08A61P7/06
CPCC07D213/81A61K31/4412A61P7/06A61P19/02A61K31/44C07D213/65A61K45/06Y02P20/55
Inventor 周云隆蔡遂雄王光凤焦玲玲闵平景羽郭明
Owner SHENYANG SUNSHINE PHARMA CO LTD
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